Executive Summary: “Damned if you do, damned if you don’t.” This is how many Florida private employers feel right now given the conflicting federal regulations and Florida’s proposed legislation concerning COVID-19 vaccine mandates. The feeling is understandable considering the federal government recently issued a new rule requiring private employers with 100 or more employees to implement COVID-19 vaccine mandates for their employees. Less than one week later, Florida proposed legislation (the “Proposed Law”) prohibiting employers from implementing mandatory vaccine policies. If Florida’s Proposed Law passes, it will be directly at odds with the federal regulations. This article will walk employers through how to handle this COVID-19 catch 22.